m-Chloroperbenzoic acid → benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide

HRID 875400Notes

Reaction equation

HRID 875400 reaction equation
N[C:2]1[C:7]2[CH:8]=[CH:9][N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:26].C(=O)(O)[O-].[Na+]>ClCCl.COC>[N:10]1([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:6]2[CH:5]=[CH:4][N+:3]([O-:26])=[CH:2][C:7]=2[CH:8]=[CH:9]1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 71061834benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 71061742benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxideYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8254Dimethyl EtherSolvent

Procedure

A stirred suspension of benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1 g, 3.9 mmol, Step a)) in a mixture of dichloromethane and dimethyl ether (10:1 mL) was treated portion wise with 3-chloroperoxybenzoic acid (0.85 g, 4.9 mmol) followed by stirring at room temperature for 4 hours. The reaction was neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to yield benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide (1 g, 99%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f71b3300e3546f49060789494e69539
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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